I like Sloan to, but I like him because he was kind of like a portal to the rabbit hole that is the dark side of the Federation. For instance Sloan says that Section 31 was created via the Federation's charter of rights or constitution, but if only a select handful (outside of Section 31) know of this agencies existence then it may imply this constitution was secretly amended.

To be honest if there was ever one group which would force the Federation government to become a dictatorship, when the going became really tough, it would be Section 31.

I think Trek's most heinous villain has to be the evil oil slick from "Skin of Evil" - it was, after all, created from all the evilness of some civilization smooshed together. Even if it was pretty crappy in execution.

I voted for the Female Changeling, but you could just as easily say the Founders as a whole. They were just so absolutely conviced that literally every other life form in the universe was inferior.

My other two votes would have been for Dukat and Soran. Soran because he was willing to kill off an entire civilization (numbering in the millions IIRC) for no other reason than to satisfy his own petty pleasure. My reasons for picking Dukat should be obvious, but special mention should be made of his creepy obsession with Kira. *shudder*

^True, but labeling anyone heinous is generally their point of view (depending on how they define it), and from a human standpoint (being that we are all human) we could call him heinous for his Romulan actions. In TNG (and DS9 too IIRC) there were moments where Romulans where desperately trying to leave that mindset. They may have been heinous to other Romulans but moral to humans.

Had to go with Annorax, oddly enough. VOY had its problems but he was one of the best Trek villains period, chillingly monstrous with a psychologically realistic core, and more truly heinous in the larger sense than Khan.

My first pick would have been Kivas Fajo -- am I going to cause angst by asking "why no Kivas Fajo"? His is a much more personal, intimate heinousness and in some ways more creepy and effective because of that; he's no world-destroying super-baddie, just a greedy, petty, pretentious sociopath, and he's all the more memorable for that.

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I agree with you--in old Trek I'm reminded of Parmen in this mold, and he was a lying sadist, but Fajo certainly had more style. His general cheerfulness was super-creepy.

I'm going to put in my own vote for Weyoun for second place: smarmy, machinating, and coldly but affably uncaring about anyone or anything else but himself and the Founders.

And 3rd...the Vidians as a species. Not evil, per se, just...heinous. I mean, we're talking Frankenstein stuff here. With live people.

-Dukat. The brilliant thing about his character was that he was given just enough humanity and awareness to make his crimes all the more wicked. He's a man who's so willingly self deluded and so obsessed with not truly examining his own sins that he actually resents the enslaved and abused people he oversees for not loving him. Someone not able to become good because he can never once question if any of his acts have been evil.

-Female Changeling. The scene that sold me was her discussion with Odo about how they have to break the solid's love of freedom and be "guided" by the Founders. The contemptuous disdain and racism towards our heroes is bad enough, but the entire War arc demonstrates how even the other species in the Dominion mean so little to her; Vorta made with no sense of aesthetics because they weren't deemed necessary, the Jem'Hadar inborn to obey their masters even when they're betrayed to their deaths; the Cardassians eventually turned cannon fodder because they aren't important. Its telling that compared to even an eventual obsessively insane megalomaniac like Dukat, she still seems more cold-hearted.

-Kivas Fajo. The genuinely sociopathic nature of the character, underneath all of his quirks make him one of the subtly darkest villains in the history of TNG. He has no empathy for anyone, only cares about his immediate personal desires, and his somewhat childish nature belies just how damn selfishly evil he is.

-Dukat. The brilliant thing about his character was that he was given just enough humanity and awareness to make his crimes all the more wicked. He's a man who's so willingly self deluded and so obsessed with not truly examining his own sins that he actually resents the enslaved and abused people he oversees for not loving him. Someone not able to become good because he can never once question if any of his acts have been evil.

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I'd like to add one other thing to your Dukat summary; toward the end, he was more like a force of chaos than any mere villain (and I mean even before he hooked up with the Pah Wraiths).